48 Products
Leeward Dress Shirt - Olive Straton Check
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Leeward Dress Shirt - Cobalt Ian Gingham
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Leeward Dress Shirt - Dark Slate Todos Plaid
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Leeward Dress Shirt - Dark Slate Banker Stripe
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Leeward Dress Shirt - Eggplant Winston Check
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Leeward Dress Shirt - Mulberry Sam Plaid
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Leeward Dress Shirt - Mulberry Dot
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Leeward No Tuck Dress Shirt - Aluminum Crew Gingham
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Leeward Formal Dress Shirt - White Solid
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Leeward Tux Dress Shirt - White Solid
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Leeward Dress Shirt - White Solid
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Leeward Formal Dress Shirt - Light Blue Solid
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The Signature Performance Dress Shirt

The Leeward is where comfort meets style. Lightweight, moisture-wicking, wrinkle-resistant, and machine washable, it’s designed for breathability and stretch so you can move freely through work, travel, or weekend plans. This is the dress shirt that started it all—for good reason.